(Colorado State University. Libraries, 2013) Jiménez-Somarribas, Alberto, author; Williams, Robert M., advisor; Wood, John L., committee member; Shi, Yian, committee member; Ladanyi, Branka M., committee member; Crick, Dean C., committee member
Documented herein are efforts towards the asymmetric total synthesis of (-)-lemonomycin, a member of the tetrahydroisoquinoline antitumor antibiotics family of natural products. We describe a concise route for the assembly of the tetracyclic core of this molecule, which involves a Pictet-Spengler reaction for the construction of the tetrahydroisoquinoline fragment and an azomethine ylide [3+2] dipolar cycloaddition for the construction of the diazabicyclo[3.2.1]octane ring system. The above-described synthetic efforts, while not totally successful, provide the basis for the future completion of the total synthesis of this natural product and other related compounds.
